How far ahead should we ask?

Two to three months for a team of fifteen or more, longer if anyone is flying.

How do we handle people who cannot do overnight stays?

Ask in the comments and plan for day attendance. It is much cheaper to know before you book the rooms.

Can I add a third option later?

Yes. Everyone who has answered is told once, in a single message.

Team offsite scheduling

For a team offsite, fix the dates before the venue: venues can usually be found for a chosen week, while twenty calendars cannot be moved to suit a chosen venue. Propose two or three candidate blocks two to three months ahead, confirm who can travel, then book. Who can when? collects the answers in one grid, free, with no account required from anyone.

Dates first, and it is not close

There is almost always another venue for the week you want. There is almost never another week that twenty people can all clear, especially once travel is involved.

So run the date poll first, with blocks rather than single days, and start venue conversations only once one block is clearly ahead.

What to put in the poll

Whole blocks, labelled by their first day: "Tue 14 - Wed 15", not two separate dates.
Two or three options, no more. Each one is a lot of logistics to hold open.
Whether travel is the night before, since that is effectively a third day for some people.
A deadline of about a week, which is realistic for people checking family commitments.
A note about who must attend, so people know whether their no is decisive.

The answers you get for free

The comments will tell you about school holidays, medical appointments and the two people who cannot do overnight stays - all things that change the plan and none of which would have come up in a room. Read them before you book rather than after.

Common questions

How far ahead should we ask?: Two to three months for a team of fifteen or more, longer if anyone is flying.
How do we handle people who cannot do overnight stays?: Ask in the comments and plan for day attendance. It is much cheaper to know before you book the rooms.
Can I add a third option later?: Yes. Everyone who has answered is told once, in a single message.

Ready when you are

Meetings and work

Getting a room full of calendars to agree without eight rounds of email.

Scheduling a team dinner Organising the team dinner? Propose a few evenings, send one link, and see who can make which. Free, no account, and the calendar invitation sends itself.
Workshop date poll A workshop needs a whole day from a lot of people. Propose a few, find out who can really give you the day, and book the room once.
Availability poll Collect availability from a whole group without collecting it one message at a time. Propose the dates, everyone marks them, and the answers add themselves up.